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The 'Wakeup Task' error is mostly attributed to the Operator not having rights to specific folders.
The Operator needs to have access to the below Named Rights:
- Prepare Delivery
- Start Deliveries
- Workflow
- Approval Administration
and the below mentioned Folders:
- Campaign Management
- Campaign Process (under Administration -> Production -> Technical workflows)
Could you try checking on these access rights and then see if Operator is able to execute the Workflow.